Konchesky signed for Charlton as a trainee in August 1997.[5] He became the youngest player to appear in the first team for Charlton (a record later broken by Jonjo Shelvey) when he played against Oxford United in August 1997 at the age of 16 years and 93 days[5][6] but it was not until the 2000–01 season when he made 27 appearances,[5] that he became a regular in the first team. In June 2003, frustrated by a lack of first-team opportunities at his preferred position of left back, Konchesky made a written request for a transfer, which was accepted by Charlton.[7] However, firm offers were not forthcoming. Instead Konchesky joined Tottenham on loan. A spate of injuries at Charlton led to Konchesky being recalled from Spurs in December 2003,[8] when he also came off the transfer list.[9]

In September 2003, Konchesky joined Tottenham Hotspur on one-month loan.[10] The loan was extended for a further month[11] and then until January 2004.[12] Although Konchesky was keen on a permanent move to Tottenham,[13] no move materialised.

Konchesky joined West Ham United in July 2005 for a fee of £1.5 million,[14] having made a total of 169 appearances for Charlton in all competitions, scoring six goals, and 15 appearances for Tottenham.[5] He made 45 league and cup appearances in the 2005–06 season,[5] helping West Ham to ninth place in the Premier League and to the 2006 FA Cup Final, where he scored when his cross went straight into the net but later had a spot kick saved as West Ham went down to Liverpool on penalties after drawing 3–3 after extra time.[15]

He lost his place in the first team to George McCartney during the 2006–07 season, making only 25 appearances[5] as West Ham slipped into the relegation places and only secured their place in the Premier League on the final day of the season. He left the club in July 2007 having made a total of 70 league and cup appearances for West Ham, scoring two goals.[5] After leaving West Ham, Konchesky criticised manager Alan Curbishley, claiming that he made the players unhappy.[16]

Konchesky signed a four-year contract with Fulham in July 2007, for a fee of up to £3.25m.[17] Konchesky played the first game of the 2008–09 season for Fulham against new Premier League team Hull City but his mistake greatly helped the opposing team score a winner after he stumbled over the ball. He missed the next game against Arsenal due to injury but returned to action the following league game against Bolton Wanderers. He scored his first goal for the club, a 35-yard piledriver into the top left hand corner of the net in January 2009 at the Boleyn Ground, in a 3–1 defeat against his former side West Ham,[18] which later won the January 2009 Goal of the Month competition and was included in the running for Goal of the Season. In September 2009, Konchesky continued his goalscoring by putting Fulham level with Everton in a 2–1 win, scoring with the aid of a deflection off Everton defender Sylvain Distin.[19] Konchesky played for Fulham in the 2009–10 Europa League final against Atlético Madrid in which Fulham were defeated after losing 2–1 from two Diego Forlán strikes.

On 27 August 2010, it was reported that Konchesky was set for a medical at Liverpool ahead of an expected move thought to be worth £3-£4 million.[20]

On 31 August 2010, Konchesky signed a four-year contract with Liverpool.[21] He made his league debut on 12 September against Birmingham City, though in the 77th minute he was injured and was substituted. He made his UEFA Europa League debut four days later in a group stage tie against Steaua Bucureşti at Anfield, with Liverpool comprehensively winning 4–1. However his time at Liverpool was a disappointment with the defender struggling at the club. An error against Spurs allowing Aaron Lennon to score the winner was heavily criticised and Konchesky was ironically cheered by Liverpool fans when substituted in the home defeat to Wolves. [22]

In January 2011, Konchesky fell out of favour after the arrival of new manager Kenny Dalglish, in his second stint as Liverpool boss, and on 31 January he joined Nottingham Forest on a 93-day emergency loan deal.[23][24] He immediately made his debut for Forest on 1 February in a 2–1 away win against Coventry City.[25] On 22 February 2011 Konchesky scored an equalising goal at home to Preston North End.[26] He played his final game for Forest on 30 April 2011 in a 5–1 win over Scunthorpe United.

Konchesky joined Leicester City for an undisclosed fee on 13 July 2011, signing a three-year contract.[27] He made his debut on 20 August 2011 in a 2–2 draw against Nottingham Forest at the City Ground, playing the full 90 minutes.[28] He scored his first league goal for the club in a 3–1 win at Burnley on 1 November 2011.[29][30] In August 2013, Konchesky was omitted from the squad and was on the verge of leaving the club,[31] but returned to the first-team after a transfer deal fell through.[32] He signed a new 18-month deal in January 2014,[33] having agreed to a substantial wage cut.[34]

Konchesky made 15 appearances for the England national under-21 football team,[35] and has two caps for the senior England team.[36] He made his England first team debut in a half-time substitution in the friendly against Australia in February 2003 and made a second appearance for England again in a half-time substitution in the friendly against Argentina in November 2005. [37]